Chief of Staff

About Rothenbury Group

Rothenbury Group is a private company managing a portfolio of businesses spanning real estate, property management, brokerage, leasing, maintenance, staffing, technology, media, and related service sectors. The group is focused on expanding its technology-driven enterprises.

Position Overview

We are seeking a senior-level Chief of Staff to partner directly with the Founder & CEO, providing leadership across multiple companies within the group. This role demands agility in a fast-paced setting where priorities frequently shift and efficient execution is paramount.

Key Responsibilities

• Convert strategic priorities into actionable execution plans.
• Coordinate cross-functional initiatives involving operations, technology, finance, legal, HR, recruitment, marketing, media, and property management sectors.
• Define ownership, set deadlines, enforce accountability, and ensure follow-ups for strategic projects.
• Maintain comprehensive visibility on ongoing projects, risk factors, delays, and operational hurdles.
• Align and hold accountable executives, managers, contractors, technology teams, and external partners.
• Lead project review rhythms, executive updates, action tracking, and subsequent follow-through.
• Support technological projects including software development, AI, CRM implementations, automations, integrations, reporting, and platform enhancement.
• Summarize executive briefings to keep the CEO informed on priorities, milestones, obstacles, and pending decisions.
• Identify opportunities to optimize workflows, communication, reporting, and operational execution.
• Develop scalable systems supporting the sustainable growth of multiple businesses.

Qualifications & Experience

• A minimum of 15 years in senior leadership roles involving executive or business operations, strategy, program management, or founder support.
• Extensive experience collaborating directly with founders, CEOs, and leadership teams.
• Background working within technology-enabled industries such as SaaS, PropTech, AI, CRM platforms, automation, or marketplaces.
• Strong knowledge of software development lifecycles, product roadmaps, and system integration projects.
• Track record of managing complex, cross-departmental initiatives effectively.
• Advanced proficiency with project management and CRM platforms like ClickUp, Jira, Asana, Monday.com, or similar.
• Exceptional organizational skills paired with effective communication and stakeholder management capabilities.
• Demonstrated discretion and sound judgment in handling confidential information.
• Bachelor’s degree required; MBA or other graduate-level degrees regarded as advantageous.

Personal Attributes

The ideal candidate excels at creating order amidst rapid change, proactively setting priorities, organizing tasks, relentlessly following up, resolving barriers, and delivering results. Comfortable engaging with diverse groups including executives, software engineers, product managers, finance and legal teams, vendors, and consultants, maintaining professionalism and urgency throughout.

Compensation & Location

Salary ranges from CAD 160,000 to CAD 180,000 annually, based on experience and fit. Additional performance-based bonuses reward project delivery, operational improvements, accountability, and overall impact. The role is primarily remote with a hybrid work model; candidates must be located in Toronto, Ontario, Canada, or nearby to attend periodic in-person meetings, trainings, or company events as needed.